Holiday rentals in Hillsdale

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Top-rated holiday rentals in Hillsdale

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Top guest favourite
The great room features a tall ceiling with a modern chandelier overhead. A cozy leather Chesterfield sofa surrounds a rustic coffee table. Large windows provide views of the lake, framed by warm-toned drapes. A fireplace adds warmth, complemented by vintage decor elements on the walls.
Cabin in Amery
5.0 out of 5 average rating, 149 reviews

Lakefront Cabin | Amazing Views | Kayaks Wildlife

Welcome to The Backwater, a newly built architect designed year-round getaway on Pike Lake in Amery, WI. Nestled in the back of a quiet, lilypad-filled bay teeming with wildlife, our cabin is the perfect destination for guests who appreciate original design and crave a unique experience. Our amenities are luxurious, but our attitude is chill inside our comfy, creative digs full of nostalgic, vintage vibes. Come stay and play on the bay while enjoying Polk Co.! Follow along @thebackwater_wi on IG

Top guest favourite
An aerial view captures the expansive Lake House Mansion overlooking a tranquil body of water. Lush greenery surrounds the property, and a spacious circular patio is visible, inviting gatherings outdoors. The clear blue sky complements the serene landscape, emphasizing the home's idyllic lakeside setting.
Home in Colfax
4.96 out of 5 average rating, 154 reviews

Mansion on Lake Tainter, sleeps 28, Jacuzzi tub

This stunning lakefront Mansion is perfect for family gatherings, reunions, weddings, and retreats, just 90 min from MSP airport, 45min from Eau Claire airport . Sleeps 20 in 5 private suites (3 kings, 2 queens) plus a kids’ bunk room; add 2 more bedrooms for 6-8 extra guests. Enjoy a chef’s kitchen, 8 fireplaces, enormous game room, 10 TVs, complimentary kayaks, and a pontoon rental available . Summer offers boating and fishing, winter brings cozy fires, sledding, ice fishing and snowmobiling.

Guest favourite
A spacious living area features warm knotty pine walls and a high ceiling adorned with large windows. A stone fireplace is centrally located, surrounded by comfortable seating and wood cabinetry. Sunlight filters through the windows, illuminating the inviting space.
Cabin in Cameron
4.93 out of 5 average rating, 56 reviews

Little Cottage On Prairie

Little Cottage on Prairie meant for relaxation! Located on Prairie Lake & Lake Chetek. Launch your boat off Wolf's Den Resort or public launch. Fish Panfish, Bass, Northern, Walleye right off cabin dock. Prairie Lake water quality is great. Knotty pine interior is tastefully decorated. Relax in front of wood burning fireplace after ice fishing or snowmobiling. Stroll down to the lake. Use kayaks of boat dock. Stargaze, roast S'mores at lake-side fire pit or the fire pit closer to the cabin.

Guest favourite
A spacious yard features a mix of pink and red seating arranged around a fire pit, surrounded by trees. The house is visible in the background, showcasing a blend of brick and wood elements with large windows that invite natural light.
Home in Rice Lake
4.83 out of 5 average rating, 109 reviews

Lake Front Home on Rice Lake: Spacious 4 Bedroom

There's something here for everyone to enjoy at this 2700 sq. ft. house. A great swimming area, a dock for boats and fishing, or attractions and activities throughout the area! This 4 bedroom, 2.5 bath lake home has all of the comforts of home with a fully-equipped kitchen, cozy furnishings, free WI-FI, a laundry, and is pet friendly. With access to the lake right outside your door. No matter the season, this home is the perfect hub for outdoor adventures: hiking, ATV's, snowmobiles, and more!

Top guest favourite
A modern cabin exterior is set against a natural backdrop, featuring large windows reflecting the surrounding greenery. A wooden deck with seating invites relaxation, and the structure showcases a sleek black facade complemented by soft landscaping.
Cabin in Comstock
4.97 out of 5 average rating, 257 reviews

Nordic Lake Cabin : Sauna/Hot Tub/Pontoon Rental

We finished building this modern Scandinavian cabin in spring 2020. It’s been featured in Vogue and on Magnolia Network. The cabin sits at the end of the road on a private lot with a perfect view of sunsets over the nature side of the lake. Drive past farm fields, into the woods, and onto our private gravel road, arriving at the driveway. Watch loons, tundra swans, eagles, beavers and deer while you relax by the lake. Pontoon boat rental is available as an add on! Pets welcome for a $90 fee!

Top guest favourite
Cabin in Almena
4.96 out of 5 average rating, 45 reviews

Lakefront Cabin · Dock · Kayaks · King BD ·Sunsets

Welcome to Sunset Cabin on Lower Turtle Lake! Outside, only steps from the water, this lakeside cabin offers a private dock, kayaks, a spacious yard, and firepit—not to mention beautiful sunsets. Inside, it comfortably sleeps 10, making it ideal for families and groups. Plan a summer fishing trip, a getaway with friends, or a trip to enjoy the many snowmobile and ATV trails. *2 King beds *2 Full/Twin bunks *Washer/Dryer *Shuffleboard *Kayaks *Games Book Now or Message With Any Questions!

Guest favourite
A modern two-story home is framed by colorful autumn trees. Large windows provide a view of the surrounding nature. A spacious deck extends from the upper level, while a fire pit area with seating is positioned on the ground level. The exterior showcases a blend of wood and stone.
Home in New Auburn
4.92 out of 5 average rating, 136 reviews

Spacious Lakefront Cabin: Sauna • Kayaks • Games

Welcome to our Perk & Pete’s! Updated 5 bedroom, 3 bathroom home with 3800 sq ft inside & over 350' of lake frontage. This beautiful property sleeps up to 10 (no more allowed due to permit restrictions). It is located on a peninsula on Tenmile lake. The house includes a fire pit area, outdoor grill, sauna, deck, patio, 4 kayaks, paddle boat & dock to maximize your time outdoors. A full kitchen, 3 fireplaces, bar, shuffleboard table & foosball table to keep you entertained inside

Top guest favourite
The charming cottage exterior features wooden siding and a sloped roof with a dormer window. Flower baskets hang from the porch posts, adding color to the serene landscape. A gravel pathway leads to the entrance, framed by natural stone landscaping and lush greenery.
Cottage in Rice Lake
4.99 out of 5 average rating, 210 reviews

Stonehaven Cottages on Tuscobia Lake LLC.

The "Gatekeeper" cottage has a natural gas stone fireplace in the living room, Full size sofa sleeper, full kitchen, full bath on the main floor and a half bath in the sleeping loft. (Need to be able to climb ladder stairs to lofted bedroom). A spiral staircase leads you down to the lower level which has an additional bedroom, queen sofa sleeper in the extra living room space, and full bathroom. The lower level also has a walk out french door to the patio area.

Guest favourite
A log cabin is framed by lush greenery, with a driveway leading to two garage doors. A pathway of stones meanders through well-kept grass, while shrubs and small plants decorate the front yard. The cabin features a covered porch, creating a welcoming entrance.
Chalet in Turtle Lake
4.9 out of 5 average rating, 110 reviews

Turtle Lodge on Upper Turtle Lake

Beautiful Log Cabin 90 minutes from the Twin Cities and steps away from prime recreational/fishing lake. Enjoy the deck overlooking lake and fire pit. In the evenings, enjoy dinner on the deck, tell stories around a campfire, savor s'mores and listen to the loons. The dock is out of the lake from Oct 1st until the week before memorial weekend. Only minutes from the ATV and Snowmobile Trails. Pontoon rental not available.

Guest favourite
Home in Cumberland
5.0 out of 5 average rating, 14 reviews

Lake Farmhouse Getaway | Game Room | Pet Friendly

The lake is 100 yards away. The arcade is upstairs. The fireplace is already on. Welcome to the Grenquist Farmhouse — Scandinavian lakeside retreat with kayaks, paddleboard, Marvel vs. Capcom arcade, vintage 1970s pinball & loft game room. Sound machines & blackout curtains in every bedroom. Pets welcome. Full kitchen, in-unit washer/dryer & 300+ mbps WiFi. 3BR/2BA sleeps 4. Cumberland, WI — 90 min from Twin Cities

Guest favourite
A spacious bedroom is highlighted by a comfortable king-sized bed adorned with colorful pillows. A ledge stone fireplace is situated near large windows, allowing natural light to fill the room. A cozy seating area with a small table is also present, enhancing the overall ambiance.
Barn in Hillsdale
4.96 out of 5 average rating, 26 reviews

The Loft Suite @ The Granary

The Loft Suite @The Granary is an ultimate retreat into luxury amid the beautiful views of the grounds. Enjoy the ultra-comfortable king-sized bed, a ledge stone fireplace, and a relaxing rainfall shower. The suite includes an atrium with a kitchenette adjacent to a main king room through spacious French doors. Many unique touches of elegant country charm. Sleeps 2.

Top guest favourite
An authentic Norwegian cabin, built with hand-hewn logs, is nestled among greenery. The structure features large windows adorned with flower boxes and a welcoming porch. A backdrop of rolling hills and trees enhances the natural setting surrounding the cabin.
Farm stay in Prairie Farm
4.97 out of 5 average rating, 145 reviews

Inga's Cabin

Step back in time. This authentic Norwegian cabin tucked in a valley among rolling hills is just 70 miles east of St. Paul. Discover the beauty of nature surrounded by hardwoods, pines and birch groves. Wander trails through 30 acres of woods and established pollinator habitat. Each season creates a fresh palette for all your senses.

Popular amenities for Hillsdale holiday rentals